Iodine → 5-Chloro-2-iodo-4-methylaniline

HRID 1777546

Reaktionsgleichung

Reaktionsgleichung von HRID 1777546
[I:1]I.[I-].[K+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[CH3:13])[NH2:9].C(=O)(O)[O-].[Na+]>O>[Cl:5][C:6]1[C:12]([CH3:13])=[CH:11][C:10]([I:1])=[C:8]([CH:7]=1)[NH2:9]

Komponenten

6

Edukt 4

HCID 807IodineHCID 4875Potassium IodideHCID 72553-Chloro-4-methylanilineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 584754055-Chloro-2-iodo-4-methylanilineAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of iodine (9.86 g; 38.84 mmol) and potassium iodide (6.45 g; 38.84 mmol) in water was added dropwise to a suspension of 3-chloro-4-methylaniline (5.00 g; 35.31 g) in a solution of sodium bicarbonate (4.75 g; 56.50 mmol). The resulting mixture was stirred for 72 hours at room temperature and filtered. The solid was dissolved in dichloromethane, washed with a saturated solution of sodium thiosulfate, and the organic layer was dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to yield 2.30 g (24%) of the title compound as a brown solid.

Aufarbeitung

  1. filtrationfiltered
  2. dissolutionThe solid was dissolved in dichloromethane
  3. washwashed with a saturated solution of sodium thiosulfate
  4. customthe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-9714f3c8b627453ca9f22efea53e7bb5
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266832B2

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